NOTE: A version of this article was posted previously on the author’s Medium page, and can be viewed here.
While web series like The Lizzie Bennet Diaries, Classic Alice and The New Adventures of Peter and Wendy have been some of the most creative modern-day adaptations of time-honored literary classics by Jane Austen, J.M. Barrie, Charles Dickens and other legendary authors, the same can definitely be said of the equally imaginative work put out by comedy troupe/production company Shipwrecked Comedy.
Co-founded by actors/writers/siblings Sean and Sinead Persaud, Shipwrecked has been among the most successful creators of hilarious literary mashups for the small screen thanks to hits like the wacky whodunit Edgar Allan Poe’s Murder Mystery Party (a.k.a. “Poe Party”), the film noir sendup The Case Of The Gilded Lily, and the scary yet silly movie trailer parody Little VVomen, which transforms Louisa May Alcott’s innocent Little Women characters (the March sisters) into diabolical young witches.
Now backed by an ongoing crowd-funding campaign through Kickstarter, Shipwrecked Comedy hopes to strike comedic gold again with their new series Headless: A Sleepy Hollow Story. Based on Washington Irving’s terrifying, oft-adapted short story The Legend of Sleepy Hollow, Headless takes Irving’s spooky tale of modest school teacher Ichabod Crane’s run from the evil Headless Horseman and puts it in an unheard-of yet instantly funny new world: that of an ensemble-based TV sitcom.
Shipwrecked is presently seeking $150,000 on Kickstarter to film Headless’ ten episodes later this year. The company is already on pace to meet that goal, having raised over $118,000 with 18 days remaining in the campaign (as of this writing). Details on the campaign, its incentives, its plans for production and more can be found on Headless’ Kickstarter page (linked to below). If the campaign meets or exceeds its goal, production of Headless will begin later this year, and the finished product will be seen on Shipwrecked’s YouTube channel (also linked to below).
In Headless, Ichabod (played by Sean Persaud, who co-wrote the series with co-star Sinead) and the Headless Horseman are living rather uncomfortably under the same roof. Despite their adversarial relationship, Ichabod and the Horseman are soon united by the former’s determination to retrieve the latter’s long-missing human head. In the midst of his search, Ichabod also discovers the importance of friendship, and the potential for greatness that’s long been inside of him.
Joining Ichabod and the Headless Horseman are Ichabod’s primarily love interest, the gorgeous heiress Katrina van Tassel (played by longtime Shipwrecked collaborator/producer Mary Kate Wiles, best known for playing Lydia Bennet in The Lizzie Bennet Diaries), whose other beau Abraham “Brom Bones” Van Brunt (Gabe Greenspan) becomes a mortal enemy to Ichabod and a player in the love triangle between all three.
Sinead portrays the vile witch Matilda Bishop, while YouTube star Jon Cozart (a.k.a. “Paint”) plays the ukulele-strumming Diedrich Knickerbocker (the alias Irving used to write his 1809 parody A History Of New York).
Fellow Shipwrecked collaborator/series producer Sarah Grace Hart (Emily Dickinson in Poe Party) co-stars as Sleepy Hollow innkeeper Lucretia Lazenby, whose lodge is populated by as many ghosts as it is flesh and blood humans, plus James Tolbert as Rip Van Winkle, Jr. (the son of Irving’s legendary long-slumbering wanderer), Krystina Arielle as Judy Gardenier, the constantly upbeat assistant to Sleepy Hollow’s mayor, Julia Cho as the town magistrate Judge Pringle, and Curt Mega and Kim Whalen as local kids’ theater managers Eugene & Ramona Trousers.
A revolving cast of actors will assume the many heads that Ichabod attempts to reattach to the decapitated Horseman, while other notable characters from The Legend Of Sleepy Hollow and Irving’s many stories (such as Rip Van Winkle) will also be featured players in Headless.
With Shipwrecked hoping to make their biggest scale production yet with Headless, the series’ filming will take place mainly in such historical landmarks as Los Angeles’ Heritage Square Museum, as well as in and around several important locations provided to Shipwrecked by The Historic House Trust of New York, cementing Shipwrecked’s attention to period-era scenic detail.
The Persauds and Wiles spoke with Snobby Robot about how they aim to pull off this ambitious project, the noticeable differences and similarities between Headless and its source material as it’s adapted for modern times, and how Headless will both entertain and inspire viewers to find out more about the works and characters of Washington Irving,
SR: This is the latest project from Shipwrecked Comedy, which has been known for producing hilarious and inventive takes on such classic novels as Little Women (for the sketch Little VVomen) and the works of famed suspense author Edgar Allan Poe (Edgar Allan Poe’s Murder Mystery Party, a.k.a. “Poe Party”). As fans of classic literature and filmmakers, what inspired you to create Headless: A Sleepy Hollow Story, which is both comedic but also faithful to the original short story and its characters even though it’s a modern adaptation of both?
Sinead Persaud (Headless producer, writer and co-star – “Matilda Bishop”): I have been a fan of the short story since I was very little. Growing up near Salem, Massachusetts, I was no stranger to living in a town that was famous for strange happenings long ago. I began writing fan fiction for the Tim Burton adaptation when I was 13 or so and always wanted to make the Headless Horseman a more comedic character. Sean and I were brainstorming and discussing possible new shows and hit upon the idea that Ichabod Crane and the Headless Horseman could be roommates! It would put a fresh modern spin on the tale that’s been done dramatically many times over.
SR: While Headless is the latest of many adaptations of Washington Irving’s The Legend Of Sleepy Hollow, this places both the short story’s iconic characters – Ichabod Crane and the Headless Horseman – in an incredibly modern sitcom setting. How did you come up with that approach to the show and those characters, and were there any sitcoms that inspired/influenced the style of Headless?
Sinead: We at Shipwrecked Comedy are extremely into mashing up genres. The idea of a legendary horror tale told in the form of a sitcom combines things we love in a fresh and entertaining way. Sean and I are, first and foremost, comedy writers who love to add dashes of the macabre and mystical to many of their works. All four of us are big sitcom fans. From Parks and Recreation to Schitt’s Creek, we wanted to give our version of Sleepy Hollow that small town ‘everybody knows your name’ sort of vibe.
What we love about those shows is that you really want to be there for those 20-30 minutes just hanging out with the zany characters and seeing what shenanigans everyone will get up to. But at their heart, they are stories about characters who grow and mature in their relationships. Sitcoms are at their best when exploring relationships, and that is what we hope to do with Headless.
SR: Discuss the process you undertook in adapting Ichabod, Headless and the source material’s other characters to the modern world in this series, and how you helped to make them – and the show itself – relatable to today’s audiences.
Sinead: The short story itself is, well…short. We took what we had, which is a fable about a man who is greedy, cowardly, and out of his depth, and tried to make it fun without sacrificing the spooky. Our Ichabod is much more likable than the Ichabod of the original tale. While he remains a lanky schoolteacher who travels to Sleepy Hollow for a new job, he’s lovable and good natured with a passion for science.
Brom Bones is often depicted as the villain of Irving’s short story, a foil to Ichabod’s cowardly frail persona. Our Brom retains some of those elements but is more comic relief. (He’s) a woke bro with a lot of soul searching to do. We’ve also taken characters from some of Washington Irving’s other tales to make Sleepy Hollow a more fully realized town. Perhaps you’ll spot a rogue Rip Van Winkle while visiting the town square. In general, we’ve tried to take the themes of the original story and relate them to things that seem relevant today.
SR: Tell me more about the show’s supporting characters, and how they’re all interconnected to both Ichabod, the Headless Horseman and the overall world of Headless.
Sean Persaud (Headless producer, writer, co-star – “Ichabod Crane”): Well, we can’t say too much but it was fun to borrow bits and pieces from Sleepy Hollow lore and beyond to create a small, spooky town full of eccentric citizens. Ichabod and the Horseman will be teaming up with some of them to form a little Scooby Gang, clashing and bickering all while trying to find the Horseman’s head.
SR: In terms of the level of production involved, the subject matter and the zany yet unique way you approach the source material, what makes Headless: A Sleepy Hollow Story both different from and similar to Shipwrecked’s previous work?
Mary Kate Wiles (series producer, co-star – “Katrina van Tassel”): Well, it’s different in that it’s our first project with a modern setting, but it’s also in a lot of ways the *most* Shipwrecked project in that it’s spooky, silly, mysterious, and based in literature. We love to mash things up, and this story combines many characters and themes from Washington Irving’s other tales into Sleepy Hollow, which of course is our main focus. This will certainly be our biggest production to date – in terms of cast, shoot days, budget, number of locations – everything.
SR: What are some of the biggest challenges that come with making a show like Headless, and how has the work you’ve done in the past prepared you for addressing the challenges of producing Headless during the ongoing COVID pandemic?
Wiles: I think on the production side, making anything for a low budget is just a giant challenge. We made Poe Party for around $60K, and we look back now and wonder how we ever accomplished that. We’re hoping to raise $150K to make Headless, and even then, it’s still not enough to really make the show we want to make and pay everyone as much as we’d like to. So we’re hoping we can exceed our goal, but we also know that no matter what happens and how much we raise, we’ll figure out how to tell the story we want to tell.
We are so lucky that so many of our friends and collaborators care deeply enough about our story that they’re willing to make some sacrifices in order to help make the best product possible. That’s how we’ve been able to create all the things we’ve done these past few years, and we’re so thankful that we have such an amazing group of collaborators in our corner.
SR: What steps are you taking to ensure a safe set while adhering to the necessary COVID protocols?
Wiles: We will have to see what the regulations for COVID safety will be by the time we’re shooting, but we’ll be following all the union guidelines for keeping everyone safe. We’re all vaccinated ourselves and we’re hoping to have a completely vaccinated cast and crew. Ideally, the pandemic will continue to improve throughout the country and filmmaking protocols will start to be inching closer to normal by the time we’re on set.
SR: In what ways do you plan to amp up the level of production quality for Headless, and how will the Kickstarter funds help to make that possible?
Wiles: Like we mentioned earlier, we’re used to making things look really cinematic on shoestring budgets, and that’s all because we have incredibly talented people lending us their skills to help bring our visions to life. We are consistently trying to move the needle so that we can start to get closer to paying our wonderful cast and crew closer to what they’re worth. Headless is also going to have our biggest cast ever – and Poe Party’s cast size was certainly fairly robust to begin with. If we can surpass our goal on Kickstarter we’ll only be able to shoot for more days, pay people better, and make a show that is as close to Sean & Sinead’s original vision as possible.
SR: Major parts of Headless’ production will take place in historic locations furnished by the Historic House Trust of New York and the Heritage Square Museum in Los Angeles. Which of these locations do you plan to film the series in, and which locations will correspond to the show’s storylines?
Wiles: We’re really excited about some of our locations that we’ll be utilizing for Headless – namely, the Heritage Square Museum here in Los Angeles. Locations can make or break a production in terms of really making the world come alive, and we’ve already been scouting pretty extensively these past few weeks to both find locations that feel like they fit into the world to us and also that we can afford on our budget.
$150K is a lot of money to us, but it can go so quickly when you’re renting out beautiful locations over a number of weeks. We’re really excited about Heritage Square and we think it’s going to provide a perfect backdrop for a number of places we need in the show. We recently hosted the Historic House Trust of New York City’s virtual gala, so we’re hoping (depending on our budget) that we might even be able to use a couple of their historic buildings on the East Coast for exteriors in the show, as well.
SR: Although Headless is a decidedly modern take on The Legend Of Sleepy Hollow, do you feel that this series will help encourage viewers to seek out the original short story, and possibly, its many filmed adaptations?
Wiles: We would love it if watching Headless encouraged viewers to seek out the original story, and who knows, maybe they won’t stop there! This is something we hope for with all of the work we’ve produced. We get so many messages from people telling us they’ve started reading H.G. Wells or George Eliot or some other author because of Poe Party, and that is just the best feeling.
That’s why we love literature – it is alive, it is constantly evolving and changing, and you can create a story now based on something that was written nearly three hundred years ago and it still resonates. It’s incredibly cool to be a part of that conversation, and we hope that we might make some of these authors proud knowing that we are helping bring their stories to a new audience. As for the filmed adaptations, sure! Ours is pretty different from any one we’ve seen yet, but that’s the fun of adaptations, isn’t it?
SR: Besides getting this show produced and available to audiences, what are your hopes for the ultimate success of Headless as both a creative project and a representation of the talents on both sides of the camera for Shipwrecked Comedy?
Wiles: We just really love this story and we can’t wait to share it with people. We feel like we’ve been able to take Irving’s short story and run with it. We love the versions of these characters we’ve been creating, and we know that our incredibly talented actor friends are going to bring them to life in such a vivid and delightful way. We are constantly looking ahead and hope that in the future we’ll be making shows for streaming services or network television, but for now we’re so excited that our audience cares enough about the sort of stories we want to tell to help us be able to tell them.
NOTE: Wiles says that should Headless’ Kickstarter campaign successfully reach or surpass its funding goal of $150,000, the ten episode series will be closed-captioned and subtitled upon its debut sometime next year on Shipwrecked Comedy’s YouTube channel.
Visit Headless’ Kickstarter campaign page here to find out more on how you can contribute to the show’s crowdfunding efforts, as well as further details on the exciting incentives available to donors at various dollar levels:
Watch all of Shipwrecked Comedy’s outstanding output, including Edgar Allan Poe’s Murder Mystery Party, on their YouTube channel:
Visit Shipwrecked Comedy’s official web site:
Check out Jon Cozart (a.k.a. “Paint”’s) YouTube channel here:
Connect with Shipwrecked Comedy on social media: